Spring brings many things; flowers and showers, of course. It’s the start of outdoor dining, of just needing a light jacket, and of festival season. Whether you’re scrolling TikTok or browsing the latest trend pieces, music festival content is everywhere. But here in the New England area, the season for a different open air activity is upon us: flea market season.

Massachusetts is home to the nation’s largest outdoor antiques and collectible fair; the six day shopping experience is a top destination for antiques aficionados–some 100,000 visitors attend each year. The 20-acre fair opens for its first run of the year in May with additional shows in July and September.

It’s not just Brimfield; rising temperatures mean flea markets all over the northeast are opening for the season. As a kid, Spring meant drives through Essex where it feels like antique stores outnumber fried fish restaurants (and that’s is really saying something.) Rummage sales, yard sales, and craft markets up and down the New England region are readying themselves for the high season and displaying their wares. Whether you’re a lifelong New Englander or visiting the region for the first time, it can still feel overwhelming: how do you know what to buy? What should you wear for a long day treasure hunting? And are there rules, unspoken or otherwise that make for a successful shopping trip?

To answer these questions, I enlisted the help of Alexander Widener, a decorator and collector who runs Widener Company an interiors store and guest cottage on the midcoast of Maine, just North of Boothbay Harbour.

Take It From The Expert

“Well, you have to wake up early!” he tells me via Zoom. “You need to get [to Brimfield] as soon as your field opens if you want to find the good stuff. I don’t really think there’s a morning routine because the morning routine is just: get there as early as you can.” He recommends grabbing a quick shower to feel fresh for what is going to be a long day, and bringing your coffee to go. Brimfield is comprised of a series of field that all have different opening times and Widener recommends planning ahead; figure out which fields you want to go to, and then build your day around that.

Antiquing can feel intimidating for new collectors or antique shoppers; there’s so much history involved in antiques and sometimes its as if the activity demands that you’re both an astute shopper and a scholar. But Widener cautions against putting up guardrails for yourself. “I think especially if you’re shopping for yourself, just go and have fun!” he says. “There are no rules; as long as you’re having fun and enjoying and buying only what really speaks to you and what you find beautiful, there are no wrong answers. You’re doing it right.” The one thing he cautions against, with a laugh, is going with someone with their eye on the same stuff you’ve got on your wishlist. “I like to go with a seasoned buddy, it’s always good to flea market with a buddy,” he says. “The key is you have to be looking or different stuff otherwise you might end up in a tiff.”

For shoppers looking to start collecting, his advice is to listen to your gut. “Sometimes this sounds so woo-woo but it might speak to you and then you’ll realize that that’s your thing.” Don’t be afraid to pick things up or to hold pieces in your hand–and never hesitate to ask questions. “I think 50% of collecting is the curiosity. What’s the story of a piece? What will I find next? Where will I put it in my home?” he says. “I think collecting is one of those things where it’s not about the outcome, it’s about the process.”

That’s not to say that the history of these objects doesn’t matter, he says–the longevity of these pieces instead can inform how we consume and our relationship with trend. “We’re all stewards of these objects,” he says. “They were here long before us and they’ll be here long after us. Trend doesn’t really come into it for me, it’s about what sparks for me and what I love, and I think that’s good advice for anyone who wants to start collecting; it doesn’t matter what other people collect, it’s about what you think is cool.”

Widener has an enviable collection of 18th century creamware; he also is always on the hunt for quilts, antique baskets, and antique gardening supplies. “I’m always looking for 19th century watering cans and wire plant stands,” he adds.

Finally, he says: consistency is key. Widener goes to Brimfield a couple times a year but he goes to his local flea market every week. “When I show up every week, I find amazing stuff.”

A Flea Market Uniform

The most important thing to remember when you’re embarking on a long day at the flea market is: leave your vanity at home. You’re going to get muddy or wet or sweaty and you don’t want to waste precious treasure hunting energy on worrying about how you look. That being said, it does feel like an incredibly chic thing to do, and far be it from me to discourage putting a cute outfit on; it’s just all about balance.

My best advice as a New Englander who navigates temperamental temperatures is your shoes are critical; Widener swears by his trusty Blundstones which are ideal for the often muddy conditions. Blundstone’s new Aerocork line includes a boot, sandal, and clog–all of which are lightweight, supportive, and so incredibly durable.

“They’re comfortable from the very first wear, and the timeless design makes them versatile enough for any outfit or occasion,” Joe Carfora, Blundstone’s Global Range Manager tells me via email. “Just as suited to beach walks and slow afternoons as they are to festivals and long evenings with friends, these styles are made to move effortlessly through your summer.” If you’re more inclined toward a sneaker, Salomon has a phenomenal selection of sneakers that don’t sacrifice style for function; similarly lightweight, I love them for long days on my feet. If you’re looking ahead to a particularly wet day, Merry People makes ankle and calf height rain boots in ultra cute colors.

When picking an outfit, I have three words for you: layer, layer, and layer; Widener agrees. “In the morning it’s cold and then once the sun comes up, it’s hot. I do shorts, and then a sweater with a T-shirt; that way I can throw the sweater over my shoulders.” I’m always partial to natural fibers as well as clothing with a little give; with a recommendation of cashmere, Widener offers a very important reminder: “Just because you’re at the flea market doesn’t mean you can’t be a little fancy!”

Retailers like Buck Mason, Donni, and Frank & Eileen all have a phenomenal selection of natural fiber knitwear and basics that are easy to wear, comfortable, and importantly, crafted to last. Donni’s Cotton Knit Roll Cardigan is one of my most-reached for items; their Rib Kick Flare or Baby Rib Scallop pant are the perfect pant if you’re looking to throw on something that feels like loungewear but looks more put together. Frank & Eileen’s Montecito and Cotswolds cardigans are likewise, beautifully made and incredibly easy to pair both with a relaxed practical outfit, and to wear out to lunch or dinner afterward. On the more affordable end of the spectrum, Banana Republic’s rustic knits made from linen, cotton, and silk are perfect for keeping warm on a chilly Spring morning; for warmer days, seersucker clothing like the selection from Marine Layer is perfect for staying cool and comfortable. If like me, you’re partial to a dress when the weather gets warmer; brands like Dôen and Christy Dawn make dresses that look just as vintage as anything you might find at the market. And look no further than Eileen West: the iconic pajama and loungewear brand just launched their first ever collection of dresses and much like the brand’s nightgown’s, they perfectly combine comfort with delicate feminine details and high quality cotton.

For chilly Spring days, choosing the right outerwear is critical and few retailers share the reputation that Barbour has for highly durable, weather tough jackets, that also happen to be incredibly sharp. Their classic Beadnell is well, a classic–and for good reason, but they make options that are both lighter and heavier weight depending on how your internal temperature runs. For warmer days, you still might want an extra layer–I recommend something lightweight like Vuori’s Ventana Jacket or a denim shirt jacket like this one from Carve Designs.

Finally, for a finishing touch: protecting your skin from the sun is a total non-negotiable; Widener also says that layering on the SPF is a must. Summer Fridays’ ShadeDrops SPF 50 Mineral Milk Sunscreen is a great choice and I also like to keep a spray, like this one from Rhode, in my bag to help me feel cool and refreshed even when I’m sweaty and covered in dust. A baseball cap or timeless straw hat is also a must–like the selection from Stetson which has traditional cowboy hats and wide, flat brim styles like panama hats. And to carry all your essentials–water, sunscreen to reapply, and cash in hand–and still leave room to stash a few trinkets that you’ve purchased along the way, a large raffia tote like the ones in the new collection from DeMellier are perfect. The bag is made using entirely plastic free raffia with stainless steel hardware for durability; and in true flea market spirit, the bags are made in small batches to minimize waste and overproduction. The brand also funds vaccines and other life saving treatments for each purchase made and they are on track to donate three million treatments by the end of 2026.

Widener also recommends a classic L.L.Bean Boat & Tote. “In my fantasy world, I’m carrying a handmade basket,” he jokes. “But in the real world I’m carrying an L.L.Bean tote because it’s light, you can put it over your shoulders, and it will literally fit anything.”

We Have (Flea Market) At Home

While people travel from all over the world to attend Brimfield, not everyone can allocate an entire trip to go flea marketing. Thankfully, plenty of large retailers and small businesses are available to shop online, whether you’re looking for candle holders, or dinnerware. Small brand Misette carries a range of table linens and glassware that look straight out of an Italian market and that will blend seamlessly with flea market finds; for a rustic feel, the Peter Dunham Collection from Hudson Grace is the way to go. “My favorite pieces are all vintage inspired,” Jaimee Seabury, the Vice President of GreenRow, tells me via email. When it comes to styling new-to-you pieces, she recommends letting your own tastes lead; it’s important to fill your home with things you love, she says, and to not get too hung up on perfection, especially when shopping vintage or antiques. “Look for timeless pieces, these will be easiest to fit in any home,” she says. “You can add special details, attach a tassel on a handle, add different hardware, or add textiles like seat cushions or sofa toppers to give a piece more character.” And antiquing and flea marketing can also inform our retail shopping; years ago, I came across vintage Ginori at a local antique store–now I collect Ginori, both old and new.

And unsurprisingly, GreenRow has a phenomenal selection of pieces that add character and elegance; glassware, like an etched decanter or a set of bud vases adds romance to any space; similarly a statement mirror or piece of rattan furniture gives the space a rustic touch. Likewise, Anthropologie has a everything from drinking glasses and vases to decorative ceramics and soft storage; I also will often opt to buy items like light fixtures new, even if they have a vintage look, because it’s something I might worry about the stability of as an antique. I’m also a big fan of Tuckernuck’s home collection which has everything from trays and baskets to And for dishes and tableware with a touch of whimsy, look no further than Rifle Paper Co.’s new garden inspired collection.